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What about the VISA situation for Canadians (to stay longer than 3 months)?

I wouldn't worry too much about Visas for Canadians, especially if you have a Bachelor's or higher in tech. I think there are several different strategies that can work to get a Visa. (This is coming from someone who was once denied a TN Visa at the US border.)

I think a B2 is good for six months; that's what I was planning to seek if our team was ever accepted, and I haven't had a problem getting them in the past whenever I traveled south on business. Of course, I would still be very interested to hear from any successful YC teams from Canada.

Although I should add that plane crossings with a return ticket seem to be much more effective at B2s than land crossings, in my experience. (B2 land crossings for me tend to include hour-long interviews in small rooms in the customs garage.)

How long in advance should someone start to look for their visa? Before applying for YC funding?

From Canada and for a B2, it's more of a wait until you've bought your tickets. Even with a TN (which I don't believe you can get with YC Funding), you just show up and hope for the best.

Of course, your mileage may vary, but this is what I've read from other people.

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